Question:

In the following reaction A is :

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Work backwards: cyclopent-1-ene carbaldehyde comes from intramolecular aldol condensation of hexane-1,6-dial, which comes from ozonolysis of cyclohexene.
Updated On: Nov 5, 2026
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The Correct Option is B

Solution and Explanation

Work backwards from the product, cyclopent-1-enecarbaldehyde.
Step (v) \(\mathrm{NaOH(aq)+\Delta}\): intramolecular aldol condensation of hexane-1,6-dial (OHC-(CH2)4-CHO) gives the five-membered ring enal.
Steps (iii)-(iv) \(\mathrm{O_3}\), \(\mathrm{(CH_3)_2S}\): reductive ozonolysis of cyclohexene gives hexane-1,6-dial.
Step (ii) alcoholic KOH: dehydrobromination of bromocyclohexane gives cyclohexene.
Step (i) \(\mathrm{Br_2, h\nu}\): free-radical bromination of cyclohexane gives bromocyclohexane.
So A = cyclohexane. Methylcyclopentane would brominate at the tertiary C and lead to a different dicarbonyl.
Answer: (2) cyclohexane
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